10070-92-5

Pyrimidine-5-carboxaldehyde is used in the preparation of (S)- and (R)-pyrimidyl alkanol by reacting with diisopropylzinc and (n-butyl)ethyl(n-hexyl)(n-propyl)methane.

Pyrimidine-5-carboxaldehyde serves as a reagent for synthesizing (E)-2-Carbamoyl-1-(naphthalene-2-yl)-3-(pyrimidin-5-yl)prop-2-en-1-one and modifying ring B structures by incorporating different pyridines[6]. The compound reacts with diisopropylzinc under asymmetric autocatalysis to produce optically active pyrimidyl alkanol[7].

Under nitrogen, a solution of 5-bromopyrimidine (1 g, 6.3 mmol) in 60 mL anhydrous THF was added BuLi (2.5 M, 2.6 mL, 6.5 mmol) at -78° C. The resulting yellow solution was stirred for 20 min, after which ethyl formate (0.55 mL, 6.7 mmol) was added dropwise over 5 min. After 20 min, the reaction was quenched with 1.5 M THF/HCl solution (4.5 mL, 6.7 mmol). The cold bath was removed, and the reaction mixture was stirred for 1 h. THF was removed in vacco, 10 mL of water was then added. The mixture was extracted with CHCl3 (2*10 mL), and the combined organics were dried (MgSO4) and concentrated. The crude product was purified via flash column chromatography (5 per cent MeOH/CHCl3) to give 0.35 g (51 per cent) of the titled Pyrimidine-5-carboxaldehyde.

[1] Journal of medicinal chemistry, 2004, vol. 47, # 20, p. 4829 - 4837
[2] Patent: US2005/70712, 2005, A1. Location in patent: Page/Page column 42
[3] Patent: US2005/171131, 2005, A1. Location in patent: Page/Page column 41
[4] Patent: US9212138, 2015, B2. Location in patent: Page/Page column 42
[5] ChemMedChem, 2017, vol. 12, # 3, p. 257 - 270